-药物合成数据库

【药物名称】

化学结构式(Chemical Structure):

参考文献No.	55376
标题:	Derivs. of p-hydroxy phenyl propionic acid as antiproliferative agents
作者:	Bermejo Barrera, J.; Hernandez Silva, M.; Alvarez de Mon, M.; Pivel Ranieri, J.P. (CSIC (Consejo Superior de Investigaciones Cient韋icas))
来源:	ES 2160093; WO 0172733

合成路线图解说明: 4-Hydroxybenzaldehyde (I) was acetylated using Ac2O in pyridine. The resultant 4-(acetyloxy)benzaldehyde (II) was then subjected to a Wadsworth-Emmons condensation with trimethyl phosphonoacetate to afford methyl 4-(acetyloxy)cinnamate (III). After catalytic double bond hydrogenation, the resultant saturated ester (IV) was reduced by LiAlH4 to furnish 3-(4-hydroxyphenyl)-1-propanol (V) 朼lternatively (V) can be obtained by reduction with LiAlH4 of the propionic acid derivative (VI) (isolated from Asplenium onopteris)-. Methylation of the phenolic hydroxyl group of (V) with iodomethane and K2CO3 in acetone gave the methyl ether (VII). Then, oxidation of alcohol (VII) to 3-(4-methoxyphenyl)propanal (VIII) was accomplished by means of pyridinium chlorochromate.

合成路线图解说明: Condensation of acetaldehyde with methyl acrylate (VIII) under Bayliss-Hillmann conditions gave rise to the allylic alcohol (IX). Bromination of (IX) using N-bromosuccinimide and dimethyl sulfide proceeded with rearrangement to the allyl bromide (X). This was then coupled with aldehyde (VII) in the presence of metallic tin and catalytic amounts of HOAc to produce, after acid-catalyzed cyclization, the target methylene butyrolactone derivative.

参考文献No.	672288
标题:	Synthesis and antiproliferative activity of a new compound containing an alpha-methylene-gamma-lactone group
作者:	Gonz醠ez, A.G.; Silva, M.H.; Padron, J.I.; Leon, F.; Reyes, E.; Alvarez-Mon, M.; Pivel, J.P.; Quintana, J.; Estevez, F.; Bermejo, J.
来源:	J Med Chem 2002,45(12),2358

合成路线图解说明: 4-Hydroxybenzaldehyde (I) was acetylated using Ac2O in pyridine. The resultant 4-(acetyloxy)benzaldehyde (II) was then subjected to a Wadsworth-Emmons condensation with trimethyl phosphonoacetate to afford methyl 4-(acetyloxy)cinnamate (III). After catalytic double bond hydrogenation, the resultant saturated ester (IV) was reduced by LiAlH4 to furnish 3-(4-hydroxyphenyl)-1-propanol (V) 朼lternatively (V) can be obtained by reduction with LiAlH4 of the propionic acid derivative (VI) (isolated from Asplenium onopteris)-. Methylation of the phenolic hydroxyl group of (V) with iodomethane and K2CO3 in acetone gave the methyl ether (VII). Then, oxidation of alcohol (VII) to 3-(4-methoxyphenyl)propanal (VIII) was accomplished by means of pyridinium chlorochromate.

合成路线图解说明: Condensation of acetaldehyde with methyl acrylate (VIII) under Bayliss-Hillmann conditions gave rise to the allylic alcohol (IX). Bromination of (IX) using N-bromosuccinimide and dimethyl sulfide proceeded with rearrangement to the allyl bromide (X). This was then coupled with aldehyde (VII) in the presence of metallic tin and catalytic amounts of HOAc to produce, after acid-catalyzed cyclization, the target methylene butyrolactone derivative.